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ChemicalBook CAS DataBase List 3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose
21870-78-0

3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose synthesis

10synthesis methods
-

Yield:21870-78-0 72% ,2774-28-9 20%

Reaction Conditions:

with sodium azide;tetrabutylammomium bromide in dimethyl sulfoxide at 20 - 80; for 10.5 h;

Steps:

(D):

General procedure: I) 1,2:5,6-Di-O-isopropylidene-3-O-(N-imidazole-1-sulfonyl)-α-D-glucofuranose (11) (1.1 g; 2.8 mmol) wasdissolved in toluene (33 ml). Tetra-N-butylammoniumbromide (2.7 g; 8.4 mmol; 3 eqv.) and NaN3 (0.55 g;8.5 mmol; 3 eqv) were added to the solution and stirred for30 min at room temperature. After the reaction mixture wasrefluxed for 10 h at 80 °C. The reaction was followed byTLC (EtOAc-hexane 1:1). After the reaction was complete,KMnO4 solution (0.45 g; 1 eqv.) was added to the reactionmixture and stirred for 5 h. The organic phase, which containedonly the main product 4 was separated and washedwith water (2 × 10 ml). The combined organic extractswere dried (Na2SO4), filtered and concentrated in vacuo toafford the product 4 as colourless oil (0.42 g; 52%). Spectraland chromatographic data of the product are in agreementwith the data of the product by (A).

References:

Nagy, Adrienn;Csordás, Barbara;Zsoldos-Mády, Virág;Pintér, István;Farkas, Viktor;Perczel, András [Amino Acids,2017,vol. 49,# 2,p. 223 - 240]